5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester → 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid

HRID 631935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631935
C([O:8][C:9]([C:11]1[N:12]([CH3:34])[N:13]=[N:14][C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=[O:10])C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[CH2:32]([O:31][C:29]([CH2:28][CH:25]1[CH2:24][CH2:23][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([C:15]3[N:14]=[N:13][N:12]([CH3:34])[C:11]=3[C:9]([OH:10])=[O:8])=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)=[O:30])[CH3:33]

Komponenten

5

Edukt 2

HCID 715003785-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl esterHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 715005385-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acidAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester (51 mg, 0.11 mmol) and 10% Pd/C (58.8 mg, 0.552 mmol) was added ethyl acetate (5 mL) at room temperature under nitrogen atmosphere. Then, the nitrogen was replaced with a hydrogen gas balloon and the black reaction mixture was stirred for 15 h under hydrogen atmosphere at which time TLC analysis indicated the absence of the starting material. Then, the reaction mixture was filtered and the charcoal was washed with a hot ethyl acetate (50 mL), THF (25 mL), CH3CN (75 mL), and ethanol (25 mL). The filtrate was concentrated under vacuum and the residue was dried under high vacuum to obtain 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (40 mg, 97.5% yield) as a white solid. LC/MS calcd. for C20H25N3O4 (m/e) 371, obsd. 372.3 [M+H, ES+].

Aufarbeitung

  1. filtrationThen, the reaction mixture was filtered
  2. washthe charcoal was washed with a hot ethyl acetate (50 mL), THF (25 mL), CH3CN (75 mL), and ethanol (25 mL)
  3. concentrationThe filtrate was concentrated under vacuum
  4. customthe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8604d89a1d04412a927d933c5f0cecf8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321738B2

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